Ingredient Details :Koaburaside


TCMI-ID: TCMI09827


Physicochemical Property
Ingredient Name Koaburaside
Pubchem CID 5318820
Iupac name (2S,3R,4S,5S,6R)-2-(4-hydroxy-3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular Formula C14H20O9
Molecular Weight 332.3
Isomeric smiles COC1=CC(=CC(=C1O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChI InChI=1S/C14H20O9/c1-20-7-3-6(4-8(21-2)10(7)16)22-14-13(19)12(18)11(17)9(5-15)23-14/h3-4,9,11-19H,5H2,1-2H3/t9-,11-,12+,13-,14-/m1/s1
InChIKey SWHCKWOYUSDWOF-RGCYKPLRSA-N
External Database Links HERB2.0: HBIN032217   SymMap: SMIT16189   TCM-ID: TCMC4681   TCMSID: 15256   ChEMBL: CHEMBL513117  
Structural Information
nHA(Number of hydrogen bond acceptors) 9
nHD(Number of hydrogen bond donors) 5
nRot(Number of rotatable bonds) 5
nRing(Number of rings) 2
MaxRing(Number of atoms in the biggest ring) 6
nHet(Number of heteroatoms) 9

Stability
nRig(Number of rigid bonds) 12
Flexibility 0.417
Stereo Centers(Number of stereocenters) 5

Solubility
TPSA(Topological polar surface area) 138.07
logS(The logarithm of aqueous solubility value) -0.83
logP(The logarithm of the n-octanol/water distribution coefficient) -0.624
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) -0.344

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.44
Synthetic accessibility score 3.497
Natural Product-likeness score 1.866
Lipinski Rule Accepted
GSK Rule Accepted
Golden Triangle Accepted

Absorption
Caco-2 Permeability -6.106
MDCK Permeability 5.78E-05
Pgp-substrate 0.274
HIA(human intestinal absorption) 0.719
F20%(20% Oral Bioavailability) 0.005
F30%(30% Oral Bioavailability) 0.809

Distribution
PPB(Plasma protein binding) 44.27%
VD(Volume Distribution) 0.505
BBB Penetration(Blood brain barrier penetration) 0.449
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 27.40%

Metabolism
CYP1A2 inhibitor 0.04
CYP1A2 substrate 0.589
CYP2C19 inhibitor 0.012
CYP2C19 substrate 0.808
CYP2C9 inhibitor 0.001
CYP2C9 substrate 0.308
CYP2D6 inhibitor 0.011
CYP2D6 substrate 0.365
CYP3A4 inhibitor 0.004
CYP3A4 substrate 0.033

Excretion
CL(The clearance of a drug) 4.384
T1/2 0.898

Toxicology
NonBiodegradable Rule 1
Pfizer Rule Accepted
SR-MMP 0.075

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.008
IGC50 1.888
LC50FM 1.901
LC50DM 3.955

Reproductive Effects
NR-AR(Androgen receptor) 0.115
NR-AR-LBD(Androgen receptor) 0.311
NR-Aromatase 0.216
NR-ER(Estrogen receptor) 0.159
NR-ER-LBD(Estrogen receptor) 0.023

Allergy
Skin Sensitization Rule 6
Skin Sensitization 0.7

Acute Toxicity
Acute Toxicity Rule 2
Rat Oral Acute Toxicity 0.008

Organ Toxicity
hERG Blockers 0.171
H-HT(The human hepatotoxicity) 0.179
DILI(Drug-induced liver injury) 0.043

Primary Irritation
Eye Corrosion 0.011
Eye Irritation 0.118
Respiratory Toxicity 0.045

Mutagenic Effects
AMES Toxicity 0.172

Tumorigenic Effects
Carcinogencity 0.1
SR-ARE(Antioxidant Response Element) 0.096
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.022
SR-p53 0.394

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